


Truth or Dare Trickster Style

by Sammynughh



Category: Supernatural
Genre: Alternate Ending, Anal Sex, Bottom Sam Winchester, Episode: s05e08 Changing Channels, Gratuitous Smut, M/M, Nipple Piercings, Oral Sex, Porn With Plot, Quid Pro Quo with the Trickster, Revealing Secret Truths, Sex Games, Sex Toys, The Trickster is a sick bastard, Top Dean Winchester, Truth or Dare, Wincest - Freeform
Language: English
Status: Completed
Published: 2018-04-19
Updated: 2018-04-19
Packaged: 2019-04-25 00:56:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14367456
Author URL: https://archiveofourown.org/users/Sammynughh/pseuds/Sammynughh
Summary: WARNING: MATURE AUDIENCES ONLYTHIS IS WINCEST!Smut! Gratuitous Smut, some angst, Trickster humor, touch of fluff.Summary: Brothers are stuck in "Changing Channels" Season 5, Episode 8. This story ends WAY differently than show canon. It's wincest. They get out of TV land eventually, but not the way they did on the show. There's a lot of sexual acts and some may seem non-consensual. The Trickster can read their thoughts and only brings out of them what he sees inside of them. They really want everything that's happening, it's just strange that it's this deity that's facilitating it.





	Truth or Dare Trickster Style

Sam and Dean are seated on one side of a rectangular table. They look around the room they're in. It looks like an old court room setting. The room is full of empty chairs in the gallery. No one in the jury box. No one at the judge's bench.

Dean stands up. "Sammy, I'm getting tired of this."

"I know. Me too."

Suddenly the Trickster comes out from the judge's chambers and takes a seat behind the judge's bench. "Okay boys. You've been going from channel to channel for several weeks. Frankly, I'm getting bored of you. So, now it's time for Truth or Dare. I'll be the judge. I'll asks the questions and give the dares. If you answer 5 questions each honestly and perform 5 dares each to completion, I will release you from this place without following you. You go back to your pathetic lives and I go back to mine. Capiche?"

Dean sits down next to his brother. He looks at Sam, "You know this is another set up."

"Of course, but what are we going to do? Say no?" Sam rolls his eyes.

The Trickster snaps his fingers and a giant score board appears. It's lit up like a Vegas slot machine. It has Sam's name on one side and Dean's on the other. It has 5 spots for T's and 5 for D's under each name.

The Trickster grins. "Each of you pick a number between 1 and 100."

Sam says, "25."

Dean says, "67."

The Trickster snaps his fingers and a wheel appears beside him with pegs on it. He spins it and it clicks against the indicator as it spins. Eventually it stops on the number 78. "Dean! You're up first! Truth or Dare?"

Dean answers quick, "Truth."

Trickster smirks. "Truth. Have you ever masturbated to thoughts of your brother Sam?"

Dean looks appalled at the question. "What?!"

"You heard me and don't lie. I know the truth." The Trickster has an arrogant smirk.

Dean swallows hard. He looks at Sam and then at his hands. He answers quietly, "Yes."

"What was that?" Trickster holds his hand to his ear.

"I said yes." Dean just glowers unable to look at Sam.

The score board overhead dings loudly and marks 1 under T's for Dean.

"Alright Sam. Your turn. Truth or Dare?" The Trickster is having way too much fun.

"Truth." Sam's nervous.

"How many guys did you have sex with in college?"

Sam asks nervously, "Does oral sex count?"

The Trickster laughs, "Duh, of course it does."

Sam thinks.

The judge gets impatient, "It's a simple question Sam."

Sam finally answers, "5."

The scoreboard chimes and Sam gets his 1 marked under his name.

Sam looks over at Dean who still hasn't looked up from his hands.

The Trickster points at Dean, "Your turn big boy. Truth or Dare?"

Dean swallows hard. "Truth."

The Trickster sighs, "Fine. Have you ever prostituted yourself for money?"

This question hit Dean hard. "Yeah. I did."

Sam looks at Dean in shock. "When?"

The judge uses his gavel on his bench. "Only the judge is allowed to ask questions."

The board chimes placings a number 2 under T's for Dean.

The judge points the gavel at Sam. "Truth or Dare?"

"Truth."

"Same question Sam. You ever whore your sweet ass for money?" He smirks.

Sam nods yes, "In college."

Dean's eyes get big as he looks at Sam. Sam just shrugs.

The board chimes for Sam giving him the number 2 under T's.

The Trickster points at Dean.

"What the hell, Dare." He's tired of the embarrassing questions.

The Trickster sits up in his seat. "I dare you to kiss your brother, and not a peck. A real kiss like you'd give a woman."

Dean glares at the deity, "You're a real sick bastard. What if I refuse?"

He laughs, "Well, you stay in TV land until forever. Frankly, I don't know what the fuss is all about. You both want each other."

While the Trickster is talking, Sam grabs hold of Dean's shoulders. "Just do it."

Dean kisses Sam. It starts off simple and they both let it become something a little bit more. As their lips part, they look into each other's eyes and a thousand unspoken words are exchanged.

"Alright you two. Break it up." The judge hits his gavel down.

The score board sounds off 1 under the D's for Dean.

The Trickster looks at Sam who's still looking at Dean. "Truth or Dare Sam?"

"Dare."

The trickster licks his bottom lip, "Jerk your brother off. Get him good and hard."

Sam squints at the Trickster. "Why are you doing this?"

"I said I'm the only one allowed to ask questions. You know you want to and he wants you to. So, do it." He moves his hand waving Sam toward Dean.

Sam approaches his brother who's already breathing hard.

Dean takes Sam's hand, "It's okay Sammy." He places it on his crotch and reaches up with his other hand to pull Sam in for a kiss.

Sam kisses Dean hard and full of want. His hand moves over Dean's bulge and then works on Dean's jean's getting them undone. Once his fly is down and he has his brother's cock out, he strokes him until he's very hard. They kiss just a little bit more before Sam backs away breathless leaving Dean hard and exposed.

Both men are very hard. Sam has his hand pressing against his own crotch trying to resituate his length. Dean places his hard length back in his underwear and jeans.

The scoreboard sounds and Sam gets 1 under his D's beneath his name.

The Trickster points at Dean. "Truth or Dare?"

"Truth." Dean can't stop looking at his brother now.

"If Sam wanted to fuck you right now, would you let him?" The Trickster has a wicked grin.

Dean looks at the judge then back at his Sammy. "I'd let him."

The scoreboard gives Dean 3 under T's.

Sam's turn.

"Dare."

The Trickster snaps and a box appears. "I dare you to use what's in that box on yourself for 5 minutes straight."

Sam opens the box and pulls out a lifesize dong and a bottle of lube. He runs a hand over his face and then through his hair. He shakes his head. "You're really fucked up. I can't believe this."

Trickster only says, "If you don't get to it, you will lose and get shoved back into TV land."

Sam undoes his pants. "Fine! I get it."

He pulls his shoes off and slips his pants off. He pulls his boxers off and uses some lube on the sex toy. He strokes his hard cock some. He then lifts his left leg up on the chair before slowly sliding the lifesize rubber cock into his ass. A timer starts counting down from 5 minutes on the giant scoreboard. Sam slowly moves the toy back and forth inside himself. He bites at his bottom lip and moans at how good it feels.

Dean has his own cock out and is stroking himself shamelessly as he watches his brother.

The five minutes runs out and Sam removes the toy with a moan setting it in the box.

The scoreboard gives Sam a 2 under the D's beneath his name.

Dean speaks up, "Dare."

Trickster almost laughs, "He's loosened up for you big boy, but not yet. You're gonna do something fun." Gabriel snaps and another box appears. "Same rules. Five minutes."

Dean opens the box and inside is a cock ring and a long metal rod. "OH HELL NO!" Dean pushes the box away.

Sam's super curious.

"Sam can assist you." He holds up his hand ready to snap. "We can end the game now with you losing."

Sam quickly looks in the box. "Dean, you can do this!"

Dean's eyes look worried. Sam kisses his brother. "Trust me." Dean nods.

Sam takes the ring from the box and stretches it onto his brother. It fits snuggly beneath his balls and around his hard cock. Dean's cock starts turning a bit red from being strangled.

Sam takes the rod into his hand and the bottle of lube from his box. He surprises Dean by first making sure they have eye contact. Once they do, Sam wraps his mouth around Dean's cock sucking him slowly.

Dean's whole body shakes. "Fuck Sammy."

Sam has Dean hard as he can get him. He takes the lubed up rod in his hand. "Okay Dean. Just take a deep breath and as I insert this breath out slowly. Most important, you need to relax. Just feel my hand on your cock. Okay?"

Dean swallows hard. "Okay." His hands are gripping the arms of the chair so tight his knuckles are white.

"Relax Dean." Sam kisses him. Dean relaxes into Sam's kiss. Sam strokes Dean's cock. "There you go. Just like that."

Sam smiles and places the tip of the lubed rod at the tip of Dean's hard cock. He strokes Dean while the rod slowly sinks inside him. Dean hisses as the cool metal rod slides inside his length. The clock started running as soon as Sam started sliding the rod inside Dean.

Sam kisses his brother as he slowly moves the rod and strokes his dick. Dean gasps into Sam's mouth. "Hold still a moment."

"You okay?" Sam touches Dean's flushed cheek."

Dean grins through his panting. "Don't wanna cum." He cups Sammy's cheek. Kisses his brother and pushes his tongue over Sam's.

Sam starts moving his hands again and Dean moans. "That feels so good."

The timer ends and Sam slowly removes the rod. A small gush of pre-cum comes out as soon as Sam removes the rod. It looks like Dean came, but he didn't. His cock is so hard and needy, it's purple.

The scoreboard gives Dean a number 2 under the D's beneath his name.

Right now Dean has 2 Dares and 3 Truths.

Sam has 2 Dares and 2 Truths.

The Trickster grins, "Sammy boy! Truth or Dare?"

Sam cringes. He hates anyone but Dean calling him Sammy. Through clinched teeth he says, "Truth."

The Trickster grins, "If Ruby was in this room right now, would you drink her blood?"

Sam looks at Dean who's still seated beside him with a hard cock. Sam looks at the Trickster, "I would. I admit I have a problem."

"That's the first step." The Trickster winks then points at the scoreboard. It sounds off. Sam gets a number 3 under his T's.

"Well fellas, looks like you're score is tied."

He looks at Dean, "It's your turn. However. I have a one time offer for you both. A Double Dare. I'll give you each 2 Dares if you let me pierce one of your nipples on each of you. You'll be wearing a barbell type piercing. I'm sure you've seen them. You can also choose to wear no jewelry and just endure the piercing." He clears his throat. "If you refuse the piercing, I'll just move on to the next..."

Dean's voice is rough. "I'll do it. Double Dare."

Sam nods, "Me too. Double Dare"

The Trickster snaps and is suddenly dressed in a doctor's outfit like on the TV show "Dr. Sexy MD". Everyone's in an operating room. Sam and Dean are sitting in dentist type chairs. Both reclined and topless.

The Trickster approaches Dean first and picks up a clamp. "Which nipple stud?"

Dean has his pants on, but the cock ring hadn't let his erection fully go away. He looks at the clamp knowing what's about to happen. He breathes a little faster. "Right side."

The room is cold, so both of Dean's nipples are hard. The trickster clamps Dean's right nipple.

He then goes to Sam and does the same to him. Same nipple.

The Trickster tells Sam, "Come watch this." Sam gets up and stands beside his brother.

The Trickster snaps and Dean's naked. His mostly hard cock resting to the side starts becoming fully hard as Dean sees Sam looking at him.

Dean bites his bottom lip nervously. Sam holds Dean's hand.

The Trickster, wearing rubber gloves, removes the clamp from Dean's nipple and pierces it right away. Dean squeezes Sam's hand. His face winces as his cock swells begging for attention. The trickster slides the barbell on while removing the needle. While attaching the ball to the other end of the barbell, the Trickster notices Dean moan. Dean has leaked a bit of pre-cum onto his abs. His cock visibly throbbing.

Sam can't take his eyes off of Dean's body. He's so breathtakingly gorgeous.

Trickster nudges Sam. "Your turn tall dark and dumbstruck."

Sam gets back on his dentist type chair and relaxes. The Trickster treats Sam the exact same way he did Dean.

Dean is now standing beside Sam and holding his hand. Sam's not at all nervous. He's anxious. No, he's eager for this. He can't wait. Sam is naked and his cock is extremely hard.

The Trickster has a needle in hand and sees Sam's raging hard on. "You like pain, don't you Sam?"

Sam smirks, "If I answer, does it count toward one of my Truths?"

The Trickster smiles, "It does."

Sam strokes his cock a couple times. "Yes, I like pain when given properly and at appropriate times."

"I guess this is an appropriate time." The Trickster removes the nipple clamp and pierces Sam's nipple quickly.

Sam arches his back and orgasms without touching his cock. Cum covers his lower abs as he pants heavily.

"Fuck Sam! No one expected that." The Trickster puts the barbell in place, removing the needle. Sam strokes his cock through his aftershocks enjoying the pleasure and the bit of pain he's feeling in his nipple.

The Trickster gets the ball attached all the way. He uses his powers to heal Sam's nipple instantly. He then pulls and plays with the piercing.

"Oh fuck!" Sam moans and arches his back. The pleasure for him is amazing.

The Trickster uses his powers to clean Sam up and he just touches Sam's balls for a moment. It freaks Sam out, but suddenly Sam has an erection again. He's recovered and ready for more.

The Trickster approaches Dean and he backs away. "Just let me heal your piercing."

Dean stands still and the Trickster heals Dean's piercing. He then does to Dean's nipple what he did to Sam's. He pulls and plays with it.

Dean gasps and grabs at the Trickster's arm. "Let go. Please." Dean's nipples are very sensitive.

The Trickster does. "Only because you said please."

"I'll make another deal with you two. One last truth from both of you and I'll send you back to your motel. Car in the parking lot. It will be like I was never here." He raises his eyebrow.

Sam's standing naked beside his brother. Both of them are semi hard and Dean still has a cockring on.

Dean says, "Agreed."

Sam says, "Fine, okay."

"Are the two of you going to have sex as soon as I drop you off?" He looks at their reactions.

Sam looks at Dean and Dean's cock hardens. Dean takes Sam's hand and Sam is hard as well. They both can't wait. They turn toward the Trickster and say together, "Yes."

The Trickster smiles. "Have fun storming the castle boys!" He snaps his fingers...

 

~~~~~

  
Sam and Dean find themselves in their motel room. They are exactly where the Trickster said he'd put them.

They sit up in bed and they are wearing what they normally wear to sleep in. Sam feels the piercing on his chest. So does Dean.

Dean also has another problem. He stands up and pulls off his underwear. He walks over to Sam's bed. "Sam, get this off of me."

Sam gets out of bed and kneels in front of Dean. He looks up at his brother and then looks at the rubber ring encasing his brother's sex. Dean's hard and getting harder the longer Sam looks at him. Sam gently pulls at the rubber ring and removes it.

Dean instantly feels relief and a surge of desire because Sam is touching him. Sam strokes Dean slowly and moves his thumb over the head of Dean's cock.

"Sam." Dean keeps eye contact as Sam spits onto Dean's cock making it nice and slick as he moves his hand over it.

Dean's losing his breath. His legs are trembling some. "Sammy." He moves his fingers through Sam's hair and Sam takes Dean into his mouth. The look on Sam's face at tasting his brother is almost enough to make him want to cum right then and there.

Sam sucks Dean perfectly.

"Fuck Sam. I'm already so close." Dean caresses Sam's jaw as he sucks a little bit more. Dean starts fucking into Sam's mouth some.

Sam releases Dean's cock and stands up. He grips Dean's face and kisses his brother.

Dean pushes Sam back while still kissing him until he's against the door. He pulls Sam's shirt off and his own. He kisses Sam and then moves his hands over Sam's bare chest. Once he gets to the piercing he only runs his hand over it. Sam gasps audibly. His cock is clearly pronounced in his pajama bottoms.

Dean places his mouth over Sam's pierced nipple and lets his tongue tease it. Sucking on his nipple while rubbing his palm over Sam's erection.

Sam bangs his head back on the door. "Fuck Dean! If you don't stop I'll cum!"

Dean stops and places his hands on either side of Sam. He presses his hard cock against Sam's clothed cock as he presses his body against Sam's. He shoves Sam harder against the door kissing his collarbone and neck. He thrusts his hips against Sam's as he nips on Sam's shoulder. "I want to be inside you so badly."

Sam pushes himself from the door and goes to his duffel. He pulls out lube and gives it to Dean. "I want you to."

Dean takes the lube.

Sam continues, "No condom. No stretching. Just use some of that and I'm good." Sam kisses Dean's neck behind his ear.

"You sure?" Dean palms Sam.

Sam removes the rest of his clothes and turns a chair around. He places his knee in the seat and bends giving Dean access to him. He looks back at his brother who's just standing there in awe of Sam's beauty. Like he's some kind of sculpted God. "Dean?"

"Oh. Yeah. I was just admiring you." Dean lubes his cock and then Sam's hole.

"Fuck me good Dean. I need it hard and fast." Sam's already panting. His cock is heavy and leaking.

Dean presses his own cock against Sam's hole and starts pushing inside. "Relax Sammy. Breathe." Dean finally gets all the way inside. He wraps his arms around Sam and kisses his shoulder. His hips moving slowly and building up speed.

"Oh God Dean. Faster!" Sam moans.

"I don't wanna come too quick Sammy. Fuck!" Dean strokes Sam's cock and he moans deep in his chest.

Dean starts moving faster while gripping Sam's hips. Skin slapping on skin echoes through the room.

After several minutes, Dean pulls out. "Turn around." Sam does and Dean kisses him. Tongue invading his mouth. Dean pushes Sam against the door again and then lifts his leg up on his arm. He enters Sam thrusting into him with quick upward movements of his hips. Sam angles his hips to get the best impact on his own prostate. "Yes Dean! Fuck me just like that!"

Dean pounds his brother hard and fast. So fast he finds himself on the edge about to climax. "Sam! Oh fuck!" Sam rubs Dean's pierced nipple on purpose and that's all it took. Dean grips Sam hard as he cums up inside him. "Sammy!"

Sam rubs his own nipple and Dean jerks Sam's cock. "Oh Dean!"

Dean moves to a position where he can suck Sam's cock and drink his brother's cum. He takes Sam deep into the back of his throat when Sam comes undone. "Oh God Dean! Fuck me!!" He cums very hard as Dean sucks down every drop.

Dean kisses his way up Sam's torso to his piercing and sucks on his nipple. Sam moans loudly and strokes his cock. "That's so good Dean. Don't stop!"

Dean swirls his tongue around the nipple and uses his teeth on the tender flesh surrounding the metal bar. He sucks on the nipple while Sam holds his brother's head to his nipple gripping his hair.

"Oh fuck! I'm cumming!" Sam strokes himself while Dean keeps sucking his nipple. Sam cums again on his own hand this time. Just not as much. "Oh my God."

Dean stands up and presses his body against Sam's. He kisses Sam, pulling some on Sam's hair. "You're mine."

Sam just nods and kisses back. "Yours. All yours Dean."

They catch their breath and take a shower. As soon as they get cleaned up, they haul ass out of town. Once they get a couple hundred miles away, they feel like they can finally breathe.

Dean taps on the steering wheel. "I think he's an angel."

Sam blinks as he's about to fall asleep, "What?"

"The Trickster. I think he's an angel. The next contact we have with him, I'm gonna trap him with holy oil. I'm gonna find out who he is."

Sam yawns. "Okay. Can we find a motel and actually sleep?"

And they do. 

 

**Author's Note:**

> Please leave a comment and kudos. I love hearing from you! ❤


End file.
